DE 196 43 007 A1 discloses adhesion promoters and adhesives based on adhesive proteins which are coupled to polymerizable plastic monomers. A preferred adhesive protein is the Mytilus edulis foot protein isolated from the byssal threads of the common mussel. Adhesion promoters and adhesives are said to be suitable for dental applications.
WO 2006/045034 discloses self-etching dental primers which contain dihydroxyphenylalanine (DOPA) combined with dilute mineral acid and optionally olefinically unsaturated monomers, aldehydes and initiators for light-curing.
U.S. 2006/0009550 discloses the preparation of hydrogels by copolymerization of aqueous mixtures of poly(ethylene glycol)diacrylate and the radically polymerizable DOPA derivatives N-methacryloyl-3,4-dihydroxy-L-phenylalanine and N-(13-(N′-t-Boc-L-3′,4′-dihydroxyphenylalaninamido)-4,7-10-trioxatridecanyl)-methacrylamide. The hydrogels are said to be suitable as surgical adhesives for medical or dental application and as carriers for delivering active ingredients to mucous membranes. It was found that DOPA derivatives exert an inhibiting effect on radical polymerization.
The synthesis of N-methacryloyl-3,4-dihydroxy-L-phenylalanine and N-(13-(N′-t-Boc-L-3′,4′-dihydroxyphenylalaninamido)-4,7-10-trioxatridecanyl)-methacrylamide is described in Lee et al., J. Biomater. Sci. Polymer Edn. 15 (2004) 449-464.
L-DOPA is the immediate biological precursor of dopamine (3,4-dihydroxyphenethylamine), a drug for the therapeutic treatment of Parkinson's disease. It is known from DE 100 82 749 T1 that L-DOPA-containing copolymers of (meth)acrylic acid release the active ingredient L-DOPA in a controlled manner. This is necessarily associated with a degradation of the polymers.
Dental materials based on dihydroxyphenylalanine derivatives which are suitable as cements, composites and coatings are not known from the state of the art.